Asymmetric formation of γ-lactams via C–H amidation enabled by chiral hydrogen-bond-donor catalysts

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Title
Asymmetric formation of γ-lactams via C–H amidation enabled by chiral hydrogen-bond-donor catalysts
Author(s)
Yoonsu Park; Sukbok Chang
Publication Date
2019-03
Journal
NATURE CATALYSIS, v.2, no.3, pp.219 - 227
Publisher
NATURE PUBLISHING GROUP
Abstract
Chiral γ-lactams are effective structural motifs found in numerous pharmaceutical agents. Despite their importance, current approaches mostly necessitate laborious synthetic steps employing pre-functionalized starting materials under demanding conditions. In this regard, asymmetric C−H amidation can provide an ideal platform for rapid construction of this valuable scaffold from unactivated materials, but unsolved issues have hampered the strategy. Here, we report iridium catalysts that overcome these challenges by utilizing chiral hydrogen-bond-donor ligands. The protocol makes use of easily accessible substrates derived from carboxylic acid, which display excellent efficiency and enantioselectivity towards direct amidation of prochiral sp 3 C−H bonds. Desymmetrization of meso-substrates is also achieved, where two consecutive stereogenic centres are selectively introduced in a single transformation. Computational investigations reveal the presence of crucial hydrogen bonding in the stereo-determining transition states and spectroscopic analysis of the structural analogues further corroborate this non-covalent interaction. © 2019, The Author(s), under exclusive licence to Springer Nature Limited
URI
https://pr.ibs.re.kr/handle/8788114/5665
ISSN
2520-1158
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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